GB1096763A - Processes for preparing steroid compounds and the compounds when thus prepared - Google Patents

Processes for preparing steroid compounds and the compounds when thus prepared

Info

Publication number
GB1096763A
GB1096763A GB51480/64A GB5148064A GB1096763A GB 1096763 A GB1096763 A GB 1096763A GB 51480/64 A GB51480/64 A GB 51480/64A GB 5148064 A GB5148064 A GB 5148064A GB 1096763 A GB1096763 A GB 1096763A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydroxy
reacting
carbon atoms
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB51480/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR890184A external-priority patent/FR1364556A/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1096763A publication Critical patent/GB1096763A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/215—Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
    • C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/38—Unsaturated compounds containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises a process for the preparation of a 13b -alkyl steroid (wherein the alkyl group contains from 2-18 carbon atoms) comprising the steps of (i) condensing a 5-oxo-6-heptenoic acid alkyl ester (wherein the alkyl group contains from 1-10 carbon atoms) with a 1,3-dioxo-2-alkylcyclopentane (wherein the alkyl group contains from 2-18 carbon atoms) in the presence of an alkaline condensation agent, and effecting cyclization and saponification of the condensation product by reaction with an acid or acid/base couple so as to form the racemic mixture of the corresponding 1,5-dioxo - 4 - (21 - carboxyethyl) - 7a - alkyl - 5,6, 7,7a-tetrahydroindane, (ii) resolving the racemic mixture by reaction with an optically active base into dextrorotatory and laevorotatory enantiomorphs, and reacting the material dextrorotatory in acetone with a mixed hydride so as to form by reduction of the keto group at the 1-position, the corresponding 1b -hydroxy-5 - oxo - 4 - (21 - carboxy - ethyl) - 7ab - alkyl-5,6,7,a-tetrahydroindane, (iii) subjecting this product to catalytic hydrogenation so as to form the corresponding 1b -hydroxy-5-oxo-4-(21 - carboxyethyl) - 7ab - alkyl - 3aa ,4b ,5,6,7, 7a-hexahydroindane, (iv) reacting this material with an acylating agent so as to form the d -lactone of the corresponding 1b -acyloxy-4-(21-carboxyethyl) - 5 - hydroxy - 7ab - alkyl - 3aa , 4b ,7,7a-tetrahydroindane, (v) reacting the d -lactone with a ketal of a 4-oxopentyl magnesium halide, reacting the product with an alkali metal base and then subjecting the resulting material to acid hydrolysis, so as to form the corresponding 17b -hydroxy-13b -alkyl-4,5-seco-gon-9-ene-3,5-dione, (vi) cyclizing this 4,5-seco-gonene in the presence of an alkali metal condensation agent so as to form the corresponding 17b -hydroxy - 13b - alkyl - gona - 4,9 - diene - 3-one and (vii) reacting this 17b -hydroxy-gonene with an acylating agent so as to form the corresponding 17b -acyloxy-13b -alkyl-gona-4,9-diene-3-one, and then effecting isomerization of this material by reaction with acyl halide having from 2 to 6 carbon atoms so as to form the corresponding 3,17b -diacyloxy-13b -alkyl-gona-1,3,5(10)-triene.
GB51480/64A 1962-03-06 1964-12-17 Processes for preparing steroid compounds and the compounds when thus prepared Expired GB1096763A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR890184A FR1364556A (en) 1962-03-06 1962-03-06 New process for the synthesis of steroids and related compounds and products used in this process
FR957460A FR1476509A (en) 1962-03-06 1963-12-17 New process for the synthesis of steroids and related compounds and products used in this process
FR960254A FR1512318A (en) 1962-03-06 1964-01-14 Optically active derivatives of 19-nor testosterone and method of preparation
FR964517A FR91612E (en) 1962-03-06 1964-02-20 Optically active derivatives of 19-nor testosterone and method of preparation

Publications (1)

Publication Number Publication Date
GB1096763A true GB1096763A (en) 1967-12-29

Family

ID=27445406

Family Applications (11)

Application Number Title Priority Date Filing Date
GB9030/63A Expired GB1042631A (en) 1962-03-06 1963-03-06 New fused polycyclic hydrocarbon derivatives and processes for the preparation thereof
GB27081/65A Expired GB1042632A (en) 1962-03-06 1963-03-06 New indane derivatives and processes for the preparation thereof
GB27082/65A Expired GB1042633A (en) 1962-03-06 1963-03-06 A new des-a-estrane derivative, and processes for its preparation
GB36333/67A Expired GB1096771A (en) 1962-03-06 1964-12-17 Novel steroid compounds
GB36204/66A Expired GB1096769A (en) 1962-03-06 1964-12-17 New 4,5-seco-gonanes and processes for their preparation
GB51480/64A Expired GB1096763A (en) 1962-03-06 1964-12-17 Processes for preparing steroid compounds and the compounds when thus prepared
GB51478/64A Expired GB1096761A (en) 1962-03-06 1964-12-17 Processes for preparing steroids compounds and the compounds when thus prepared
GB51479/64A Expired GB1096762A (en) 1962-03-06 1964-12-17 Processes for preparing steroids compounds and the compounds when thus prepared
GB51481/64A Expired GB1057117A (en) 1962-03-06 1964-12-17 Processes for preparing steroids compounds and the compounds when thus prepared
GB36202/66A Expired GB1096767A (en) 1962-03-06 1964-12-17 New indane derivatives, processes for their preparation, and the derivatives when thus prepared
GB36203/66A Expired GB1096768A (en) 1962-03-06 1964-12-17 New indane derivatives, processes for their preparation, and the derivatives when thus prepared

Family Applications Before (5)

Application Number Title Priority Date Filing Date
GB9030/63A Expired GB1042631A (en) 1962-03-06 1963-03-06 New fused polycyclic hydrocarbon derivatives and processes for the preparation thereof
GB27081/65A Expired GB1042632A (en) 1962-03-06 1963-03-06 New indane derivatives and processes for the preparation thereof
GB27082/65A Expired GB1042633A (en) 1962-03-06 1963-03-06 A new des-a-estrane derivative, and processes for its preparation
GB36333/67A Expired GB1096771A (en) 1962-03-06 1964-12-17 Novel steroid compounds
GB36204/66A Expired GB1096769A (en) 1962-03-06 1964-12-17 New 4,5-seco-gonanes and processes for their preparation

Family Applications After (5)

Application Number Title Priority Date Filing Date
GB51478/64A Expired GB1096761A (en) 1962-03-06 1964-12-17 Processes for preparing steroids compounds and the compounds when thus prepared
GB51479/64A Expired GB1096762A (en) 1962-03-06 1964-12-17 Processes for preparing steroids compounds and the compounds when thus prepared
GB51481/64A Expired GB1057117A (en) 1962-03-06 1964-12-17 Processes for preparing steroids compounds and the compounds when thus prepared
GB36202/66A Expired GB1096767A (en) 1962-03-06 1964-12-17 New indane derivatives, processes for their preparation, and the derivatives when thus prepared
GB36203/66A Expired GB1096768A (en) 1962-03-06 1964-12-17 New indane derivatives, processes for their preparation, and the derivatives when thus prepared

Country Status (11)

Country Link
US (1) US3413314A (en)
BE (4) BE657261A (en)
BR (5) BR6347416D0 (en)
CH (10) CH433265A (en)
DE (7) DE1468530A1 (en)
DK (7) DK114687B (en)
FR (3) FR1476509A (en)
GB (11) GB1042631A (en)
IL (6) IL22635A (en)
NL (8) NL6414756A (en)
SE (5) SE310364B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1526962A (en) * 1967-01-06 1968-05-31 Roussel Uclaf New process for preparing a gonatrienic compound and resulting products
US3979458A (en) * 1967-12-04 1976-09-07 Syntex Corporation Production of unsaturated carbocyclic ketones
US3855247A (en) * 1967-12-04 1974-12-17 Syntex Corp Production of unsaturated carbocyclic ketones
US3541210A (en) * 1968-04-10 1970-11-17 Sandoz Ag 17-alpha-(2-butyn-1-yl)-substituted steroids
US3929876A (en) * 1968-10-04 1975-12-30 Hoffmann La Roche Stereospecific total steroidal synthesis via substituted C/D-trans indanones
US3927031A (en) * 1968-10-04 1975-12-16 Hoffmann La Roche Stereospecific total steroidal synthesis via substituted C/D-trans indanones
US3897460A (en) * 1968-10-04 1975-07-29 Hoffmann La Roche 3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes
FR2183555B1 (en) * 1972-05-10 1975-06-20 Roussel Uclaf
US4158012A (en) * 1978-06-19 1979-06-12 Syntex (U.S.A.) Inc. Steroid synthesis process using mixed anhydride
US4234491A (en) 1978-06-19 1980-11-18 Syntex (U.S.A.) Inc. Steroid synthesis process using mixed anhydride
US4400524A (en) * 1981-07-28 1983-08-23 The Upjohn Company Grignard reagents prepared from 5-halopentan-2-one propylene ketals
US4900837A (en) * 1982-05-18 1990-02-13 University Of Florida Brain-specific drug delivery of steroid sex hormones cleaved from pyridinium carboxylates and dihydro-pyridine carboxylate precursors
US5567830A (en) * 1994-02-14 1996-10-22 Cocensys, Inc. Process for synthesis of acetylenic carbinols
DE19503327A1 (en) * 1995-02-02 1996-08-08 Basf Ag Process for the preparation of 5-oxo-6-heptenoic acid alkyl esters and new intermediates for their preparation
IL119649A (en) * 1995-11-30 2002-03-10 Akzo Nobel Nv Preparation of cyclic ketals of 3-keto-5(10), 9(11)-steroid diene derivatives
ITUB20155260A1 (en) 2015-10-30 2017-04-30 Ind Chimica Srl PROCESS FOR THE PREPARATION OF 17? -Hydroxy-des-A-androst-9,10-en-5-one

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE632347A (en) *
US2839537A (en) * 1952-05-12 1958-06-17 Ciba Pharm Prod Inc Tricyclic diketone and process of manufacture
US3019252A (en) * 1959-06-18 1962-01-30 Lab Francais Chimiotherapie Process for the preparation of novel derivatives of cyclopentanonaphthalene and products obtained thereby
US3115507A (en) * 1960-01-22 1963-12-24 Roussel Uclaf New analogs of 19-nor-testosterone, their esters and process of preparation
FR1363113A (en) * 1960-07-29 1964-06-12 Roussel Uclaf New estradienic derivatives
FR1283951A (en) * 1960-12-28 1962-02-09 Chimiotherapie Lab Franc New propyl derivative of phenanthrene and method of preparation

Also Published As

Publication number Publication date
IL30735A (en) 1970-12-24
DK111956B (en) 1968-10-28
BR6465401D0 (en) 1973-07-17
CH424768A (en) 1966-11-30
NL6414702A (en) 1965-06-18
GB1042632A (en) 1966-09-14
BR6465402D0 (en) 1973-07-17
DE1468897A1 (en) 1969-01-02
DE1468895A1 (en) 1969-01-23
DE1468529C3 (en) 1979-10-31
SE302301B (en) 1968-07-15
BE657262A (en)
FR91612E (en) 1968-07-19
CH436273A (en) 1967-05-31
IL30736A (en) 1969-01-29
GB1096769A (en) 1967-12-29
GB1042633A (en) 1966-09-14
FR1512318A (en) 1968-02-09
DE1468529B2 (en) 1979-03-08
SE319174B (en) 1970-01-12
GB1042631A (en) 1966-09-14
DE1518111B2 (en) 1978-08-31
DE1468529A1 (en) 1969-04-10
GB1096767A (en) 1967-12-29
DE1468530C3 (en) 1979-12-20
NL123143C (en)
IL22636A (en) 1968-12-26
CH433265A (en) 1967-04-15
IL22637A (en) 1969-02-27
GB1096761A (en) 1967-12-29
IL22635A (en) 1969-01-29
BE657261A (en)
FR1476509A (en) 1967-04-14
NL122309C (en)
BE657263A (en)
DK144794C (en) 1982-12-20
IL22638A (en) 1969-03-27
DE1468896A1 (en) 1969-01-16
SE309038B (en) 1969-03-10
DK112032B (en) 1968-11-04
DK121224B (en) 1971-09-27
DE1468897C3 (en) 1978-07-13
DE1518111A1 (en) 1972-03-16
DE1468531B1 (en) 1977-03-31
GB1096771A (en) 1967-12-29
DK144794B (en) 1982-06-07
NL6414756A (en) 1965-06-18
GB1096762A (en) 1967-12-29
SE310364B (en) 1969-04-28
NL126395C (en)
CH410934A (en) 1966-04-15
GB1057117A (en) 1967-02-01
NL6414755A (en) 1965-06-18
DK127062B (en) 1973-09-17
DK114131B (en) 1969-06-02
BE657260A (en)
NL122142C (en)
BR6565404D0 (en) 1973-08-02
DE1468530A1 (en) 1969-03-06
CH437272A (en) 1967-06-15
CH411858A (en) 1966-04-30
CH436274A (en) 1967-05-31
CH450406A (en) 1968-01-31
DK114687B (en) 1969-07-28
CH427782A (en) 1967-01-15
BR6347416D0 (en) 1973-08-28
GB1096768A (en) 1967-12-29
US3413314A (en) 1968-11-26
BR6465403D0 (en) 1973-08-02
CH436275A (en) 1967-05-31
DE1468530B2 (en) 1979-03-22
SE313306B (en) 1969-08-11
NL6414764A (en) 1965-06-18
DE1518111C3 (en) 1979-04-26

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